Ugi four-component condensation with two cleavable components: the easiest synthesis of 2,N-diarylglycines

Tetrahedron Letters

Volumn 49, Issue 13, 2008, Pages 2099-2102

  Faggi, Cristina ^a   Neo, Ana G ^a,b   Marcaccini, Stefano ^a   Menchi, Gloria ^a   Revuelta, Julia ^a,c  

^a UNIVERSITY OF FLORENCE   (Italy)

^b UNIVERSITY OF EXTREMADURA   (Spain)

^c INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

2, N DIARYLGLYCINE DERIVATIVE; ALDEHYDE DERIVATIVE; ANILINE DERIVATIVE; CYANIDE; GLYCINE DERIVATIVE; OXOACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; POLYMERIZATION; SYNTHESIS;

EID: 39649122095     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.01.134     Document Type: Article

References (19)

1. Dömling A., and Ugi I. Angew. Chem., Int. Ed. 39 (2000) 3168-3210
2. Marcaccini S., and Torroba T. In: Zhu J., and Bienaymé H. (Eds). Multicomponent Reactions (2005), VCH, Weinheim 33-75
3. Dömling A. Chem. Rev. 106 (2006) 17-89
4. Ugi I., and Rosendahl F.K. Liebigs Ann. Chem. 666 (1963) 65-67
5. Keating T.A., and Armstrong R.W. J. Am. Chem. Soc. 117 (1995) 7842-7843
6. J. Am. Chem. Soc. 118 (1996) 2574-2583
7. Rikimaru K., Yanagisawa A., Kan T., and Fukuyama T. Synlett (2004) 41-44
8. Alcaide B., Almendros P., and Aragoncillo C. Chem. Eur. J. 8 (2002) 3646-3652
9. Groebke Zbinden K., Obst-Sander U., Hilpert K., Kühne H., Banner D.W., Böhm H.-J., Stahl M., Ackermann J., Alig L., Weber L., Wessel H.P., Riederer M.A., Tschopp T.B., and Lavé T. Bioorg. Med. Chem. Lett. 15 (2005) 5344-5352
10. Ugi I., and Fetzer U. Chem. Ber. 94 (1961) 1116-1121
11. The Ugi 4-CC adducts prepared from pyruvic acid are more soluble in methanol than the corresponding adducts arising from benzoylformic acid. Thus, lower overall yields of α-amino acids were obtained when the cleavage was performed on the isolated Ugi adducts.
12. 3 (30 ml). The layers were separated and the aqueous phase was acidified with formic acid until pH 4. The resulting suspension was filtered and the collected solid product washed with water and dried to give almost pure 7 in 87-93% yield.
13. 2 provided by shelxl97 [Sheldrick, G. M. shelxl97: Program for Crystal Structure Refinement; Institut für Anorganische Chemie der Universität Göttingen: Göttingen, Germany]. The non-hydrogen atoms were refined anisotropically; aromatic and methylenic hydrogens were assigned in calculated positions, whereas hydrogens on C(22) and O(3) were found in the Fourier synthesis; all of them were refined as isotropic. The X-ray CIF file for this structure has been deposited at the Cambridge Crystallographic Data Center with the deposition number CCDC 616531. Copies of the data can be obtained, free of charge, from CCDC, 12 Union Road, Cambridge, CB2 1EZ UK (e-mail: deposit@ccdc.cam.ac.uk, internet: www.ccdc.cam.ac.uk).
14. Both carbonyl groups are reactive enough to undergo base-promoted nucleophilic attacks by the amide nitrogen. The formation of orthoamides from Ugi-4CC adducts has been reported:. Marcaccini S., Miguel D., Torroba T., and García-Valverde M. J. Org. Chem. 68 (2003) 3315-3318
15. For another example of the reactivity of Ugi-4CC adducts with additional carbonyl groups:. García-Valverde M., Macho S., Marcaccini S., Rodríguez T., Rojo J., and Torroba T. Synlett (2008) 33-36
16. To our knowledge only an example has been reported in which a saturated, unfunctionalized isocyanide behaves as a C1 synthon:. Henkel B., and Weber L. Synlett (2002) 1877-1879
17. Recently a simple solution-phase access to these compounds based on the method of Henkel and Weber has been reported. See Ref. 6.
18. See for example:. Csongar C., Mueller I., Slezak H., Klebsch H.-J., and Tomaschewski G. J. Prakt. Chem. 330 (1988) 1006-1014
19. Arshady R., and Ugi I. Polymer 31 (1990) 1164-1169